WO2023212495A1 - Nouveau composé d'origine biologique, procédé de formation du composé et compositions adhésives contenant le nouveau composé - Google Patents

Nouveau composé d'origine biologique, procédé de formation du composé et compositions adhésives contenant le nouveau composé Download PDF

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Publication number
WO2023212495A1
WO2023212495A1 PCT/US2023/065944 US2023065944W WO2023212495A1 WO 2023212495 A1 WO2023212495 A1 WO 2023212495A1 US 2023065944 W US2023065944 W US 2023065944W WO 2023212495 A1 WO2023212495 A1 WO 2023212495A1
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WIPO (PCT)
Prior art keywords
compound
independently
formula
alkyl
amino acid
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PCT/US2023/065944
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English (en)
Inventor
Mavyn Holman
Nandita BHAGWAT
Yan Meng
Ke Li
Jason Patrick SAFKO
Christopher HORNAT
Matthew Hernandez
Md Nazim UDDIN
Ranga Ranganathan
Christie SUTANTO
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Zymergen Inc.
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Publication of WO2023212495A1 publication Critical patent/WO2023212495A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/26—Di-epoxy compounds heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3236—Heterocylic compounds
    • C08G59/3245—Heterocylic compounds containing only nitrogen as a heteroatom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5033—Amines aromatic

Definitions

  • the present disclosure relates to novel bio-based compounds and adhesive compositions containing the novel compounds.
  • Adhesives are highly desirable in many applications, particularly for optical displays and electronics. As electronic devices become smaller and smaller, new challenges arise on the adhesives, such as higher performance in a smaller and tighter space.
  • a compound in one embodiment, can have a structure of formula (1) or formula(2): with Rl, R2 being independently H, or alkyl, or alkylaryl, or XI, or X2;
  • Y 1 being C1-C5 alkyl or isoalkyl
  • Y3 being H or C1-C3 alkyl
  • n being 1-10.
  • an adhesive composition can comprise at least one compound having a structure of formula (1) or formula (2): with Rl, R2 being independently H, or alkyl, or alkylaryl, or XI, or X2;
  • Y 1 being C1-C5 alkyl or isoalkyl
  • Y3 being H or C1-C3 alkyl
  • n being 1-10.
  • a method of forming a compound can comprise: forming an amino acid dimer of an amino acid; alkoxylating the amino acid dimer with an alkyl oxide to form an alkoxylated amino acid dimer; and introducing at least one functional group on the alkoxylated amino acid dimer, the functional group being selected from hydroxyl, epoxy, acrylate, alkylacrylate, or isocyanate, wherein the compound has a structure of formula (1) or formula (2): with Rl, R2 being independently H, or alkyl, or alkylaryl, or XI, or X2;
  • Y 1 being C1-C5 alkyl or isoalkyl
  • Y3 being H or C1-C3 alkyl
  • n being 1-10.
  • FIG. 1 includes a scheme illustrating a method of making the novel bio-based compound according to one embodiment.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
  • a process, method, article, or apparatus that comprises a list of features is not necessarily limited only to those features but may include other features not expressly listed or inherent to such process, method, article, or apparatus.
  • the present disclosure is directed to a novel compound falling under formula (1) or (2) described above.
  • the compound falling under formula (1) or (2) is interchangeable also called “functionalized cyclic amino acid dimer” of the present disclosure.
  • a method of making the compound of the present disclosure can include: forming a cyclic amino acid dimer of an amino acid (11); alkoxylating the amino acid dimer with an alkoxyl oxide to form an alkoxylated amino acid dimer (12); and introducing at least one functional group on the alkoxylated amino acid dimer (13).
  • the amino acid for forming the amino acid dimer (step 11) can be selected from tyrosine, hydroxyproline, phenylalanine, or glycine.
  • alkoxylating the amino acid dimer (step 12) to an alkoxylated amino acid dimer can be conducted by reacting the hydroxyl groups and amine groups of the amino acid dimer with an alkyloxide selected from the group of ethylene oxide, propylene oxide, or butylene oxide.
  • the alkyloxide can be propylene oxide.
  • the alkoxylated amino acid dimer can be subjected to further introducing at least one functional group.
  • the at least one functional group can be a hydroxyl group, an epoxy group, an acrylate group, an alkylacrylate group, or an isocyanate group.
  • the alkoxylated amino acid dimer can be functionalized by introducing one or more epoxy groups, also called herein epoxidation.
  • the epoxidation reaction can be stoichiometric, such that one mole of epichlorohydrin or epibromohydrin is used per mole of hydroxy groups in the moiety.
  • the molar ratio of epoxidizing agent to hydroxy groups of the alkoxylated amino acid dimer can vary within a range from 20: 1 to 0.9: 1, such as from 15:1 to 1: 1, 10: 1 to 1 : 1, or 5:1 to 1: 1.
  • the compound of the present disclosure can have a structure of formula (3): with R1 and R2 being independently H, or alkyl, or alkylaryl; and Zl, Z2 being independently hydroxyl, epoxy, acrylate, methacrylate, or isocyanate; and n, m being 1-10.
  • the compound may have a structure of formula (4):
  • the compounds of the present disclosure may have the structure of formula (5): , or hydrogen, or alkyl, or alkylaryl;
  • the compound can have the structure of formula (6), with n, m, x, y independently being 1-10.
  • the compound of the present disclosure can have the structure of formula (7): independently being 1-10.
  • the compound of the present disclosure can have a bio-based carbon content of at least 10%, such as at least 15%, at least 20%, at least 25%, at least 30%, or at least 35%, as determined by ASTM D6866.
  • Bio-based carbon content as defined herein is the percentage of carbons from renewable or biogenic sources, such as plants or animals over the total number of carbons in the compound.
  • the present disclosure is further directed to an adhesive composition comprising the compound falling under formula (1) or (2) as described in embodiments above, or a combination thereof.
  • the amount of the compound of formula (1) or (2) in the adhesive composition can be at least 5 wt% based on the total weight of the adhesive composition, such as at least 10 wt%, at least 20 wt%, at least 30 wt%, at least 40 wt%, or at least 50 wt%, or at least 55 wt%. In another aspect, the amount of the compound in the adhesive composition may be not greater than 70 wt% based on the total weight of the adhesive composition, such as not greater than 60 wt%, or not greater than 55 wt%, or not greater than 50 wt%.
  • the adhesive composition can include next to the compound of formula (1) or (2) at least one second compound, wherein the at least one second compound is adapted to react with the functional groups of the compound of formula (1) or (2).
  • the second compound can be an amine compound.
  • the amine compound may includes m-xylenediamine or 1,13 diamino-4,7,10 trioxatridecane.
  • the adhesive composition can include one or more further additives, for example, a solvent, a filler, a dye, a viscosity modifying agent, a dispersing agent, or a curing initiator.
  • a solvent for example, a solvent, a filler, a dye, a viscosity modifying agent, a dispersing agent, or a curing initiator.
  • the use of the compound of the present disclosure in adhesive compositions can have an advantage to obtain adhesives having improved lap shear strength, elongation, and impact resistance without compromising the glass transition temperature.
  • the use of the compound of the present disclosure may not be limited to adhesives, but the compound can be also employed in a composite, a coating, an electronic device, an energy storage device, or an energy generation device.
  • Embodiment 1 A compound having a structure of formula (1) or formula(2): with Rl, R2 being independently H, or alkyl, or alkylaryl, or XI, or X2;
  • Y 1 being C1-C5 alkyl or isoalkyl
  • Y3 being H or C1-C3 alkyl
  • n being 1-10.
  • Embodiment 2 The compound of embodiment 1, having the structure of formula (3): with R1 and R2 being independently H, or alkyl, or alkylaryl; and
  • Zl, Z2 being independently hydroxyl, epoxy, acrylate, methacrylate, or isocyanate; and n, m being 1-10.
  • Embodiment 3 The compound of embodiment 2, comprising a structure of formula (4): with n, m independently being 1-10.
  • Embodiment 4 The compound of embodiment 1, having the structure of formula (5): with R3 or R4 being , or hydrogen, or alkyl, or alkylaryl;
  • Zl, Z2 being independently hydroxyl, epoxy, acrylate, methacrylate, or isocyanate; and n, m independently being 1-10.
  • Embodiment 5 The compound of embodiment 4, comprising a structure of formula (6): with n, m, x, y independently being 1-10.
  • Embodiment 6 The compound of embodiment 1, comprising a structure of formula (7): with n, m independently being 1-10.
  • Embodiment 7 An adhesive composition comprising at least one compound having a structure of formula (1) or formula (2): with Rl, R2 being independently H, or alkyl, or alkylaryl, or XI, or X2;
  • Y 1 being C1-C5 alkyl or isoalkyl
  • Y3 being H or C1-C3 alkyl
  • n being 1-10.
  • Embodiment 8 The adhesive composition of embodiment 7, the adhesive composition comprising a compound having a structure of formula (3): with R1 and R2 being independently H, or alkyl, or alkylaryl; and Zl, Z2 being independently hydroxyl, epoxy, acrylate, methacrylate, or isocyanate; and n, m being 1-10.
  • Embodiment 9 The adhesive composition of embodiment 8, wherein the adhesive composition comprises a compound having a structure of formula (4): with n, m independently being 1-10.
  • Embodiment 10 The adhesive composition of embodiment 7, comprising a compound having a structure of formula (5):
  • Zl, Z2 being independently hydroxyl, epoxy, acrylate, methacrylate, or isocyanate; and n, m independently being 1-10.
  • Embodiment 11 The adhesive composition of embodiment 10, wherein the adhesive composition comprises a compound having a structure of formula (6): with n, m, x, y independently being 1-10.
  • Embodiment 12 The adhesive composition of embodiment 7, comprising a structure of formula (7): with n, m independently being 1-10.
  • Embodiment 13 The adhesive composition of any one of embodiments 7-12, wherein the adhesive composition further comprises an amine compound.
  • Embodiment 14 The adhesive composition of embodiment 13, wherein the amine compound includes m-xylenediamine or 1,13 diamino-4,7,10 trioxatridecane.
  • Embodiment 15 A method of forming a compound, comprising: forming an amino acid dimer of an amino acid; alkoxylating the amino acid dimer with an alkyl oxide to form an alkoxylated amino acid dimer; and introducing at least one functional group on the alkoxylated amino acid dimer, the functional group being selected from hydroxyl, epoxy, acrylate, alkylacrylate, or isocyanate.
  • Embodiment 16 The method of embodiment 15, wherein the amino acid is selected from tyrosine, hydroxyproline, or glycine.
  • Embodiment 17 The method of embodiments 15 or 16, wherein the alkyloxide is selected from ethylene oxide, propylene oxide or butylene oxide.
  • Embodiment 18 The method of embodiment 17, wherein the alkyl oxide comprises propylene oxide.
  • Embodiment 19 The method of any one of embodiments 15-18, wherein the functional group is an epoxy group.
  • Embodiment 20 The method of embodiment 19, wherein introducing the at least one epoxy group comprises reacting the alkoxylated amino acid dimer with epichlorohydrine.
  • Embodiment 21 The method of any one of embodiments 15-20, wherein the compound has a structure of formula(l) or formula (2): with Rl, R2 being independently H, or alkyl, or alkylaryl, or XI, or X2;
  • Y 1 being C1-C5 alkyl or isoalkyl
  • Y3 being H or C1-C3 alkyl
  • n being 1-10.
  • Embodiment 22 The method of embodiment 21, wherein the compound has a structure of formula (3): with R1 and R2 being independently H, or alkyl, or alkylaryl; and
  • Embodiment 23 The compound of embodiment 22, wherein the compound has a structure of formula (4): with n, m independently being 1-10.
  • Embodiment 24 The method of embodiment 21, wherein the compound has a structure of formula (5): with R3 or R4 being , or hydrogen, or alkyl, or alkylaryl;
  • Zl, Z2 being independently hydroxyl, epoxy, acrylate, methacrylate, or isocyanate; and n, m independently being 1-10.
  • Embodiment 25 The method of embodiment 24, wherein the compound has a structure of formula (6): with n, m, x, y independently being 1-10.
  • Embodiment 26 The method of embodiment 21, wherein the compound has a structure of formula (7): with n, m independently being 1-10.
  • the amino-acid dimer of tyrosine was made by mixing 200 g of tyrosine and 800 ml ethylene glycol in a 3L two-neck round bottom flask equipped with magnetic stirrer and overhead condenser. The flask was heated with an oil bath to 190 °C and the reaction mixture was stirred for 7h at this temperature. The conversion of starting material to the dimer was followed up by HPLC. After cooling the reaction mixture down to room temperature, the precipitated solid was filtered and washed with ethanol (2x 200ml). The solid was dried in a vacuum oven. The yield of the tyrosine amino acid dimer (TAD) was 64%.
  • the TAD was propoxylated according to the following procedure: In a reaction vessel, 16.32 g of TAD, 13.821 g of potassium carbonate, and 100 ml dimethyl sulfoxide were added and stirred under nitrogen for about 15 minutes. Thereafter, 11.61 g of propylene oxide was added to the reactor and the reaction mixture heated to 100°C and held at this temperature for about 5 hours.
  • reaction product was discharged from the reactor into a separatory funnel where it was neutralized with 12.6 Molar hydrochloric acid. After reaching a pH between 6-7, the product was washed by rinsing three times with dichloromethane (DCM). The DCM containing layer was separated from the aqueous layer, washed with deioinized water three times, followed by washing three times with brine, drying with magnesium sulfate and filtering. Thereafter, the DCM was removed by rotary evaporation and the remaining product dried overnight under vacuum at a temperature between 80-90°C.
  • DCM dichloromethane
  • reaction equation R11-A A summary of the conducted reaction is shown in reaction equation R11-A below.
  • the dimer of amino acid of phenylalanine was synthesized and propoxylated.
  • the phenylanaline amino acid dimer (PAD) was propoxylated using 10.30 g PAD, 0.191 g KOH, 100 ml DMSO, and 4.27 g propylene oxide. See also reaction equation R14-A below.
  • the propoxylated amino acid dimers of Example 1 were further subjected to a diglycidilation reaction according to the following general procedure: 0.1 eq of tetrabutylammonium hydrogen sulfate (Bu4NHSO4) and 10 eq of solid sodium hydroxide (NaOH) were added to a round bottom flask and stirred under nitrogen. Thereafter, a solution of
  • the epoxy equivalent weight (EEW) was calculated according to ASTM DI 652-11.
  • the compounds were tested via modulated differential scanning calorimetry (MDSC) and the first and second heat peak recorded.
  • MDSC modulated differential scanning calorimetry
  • Table 1 shows a summary of the test results, together with the results of commercial product E828, a difunctional bisphenol A- epichlorohydrin, which is a known amine-reactive adhesive component, and used as comparative sample.
  • Adhesive compositions were prepared with each of the epoxy compound listed in Table 1, by combining 1: 1 volume equivalents of epoxy compound with m-xylenediamine (mXDA).
  • Curing of the adhesive compositions was conducted by heating for 1 hour at 70°C, followed by heating for 2 hours at 175°C.
  • Table 2 summarizes measured properties of the adhesive compositions, such as cure peak enthalpy, cure peak temperature, glass transition temperature (tan 8 of storage modulus curve) and storage modulus at 25 °C (approximate room temperature modulus) and 200 °C (rubbery state modulus, which gives a measure of crosslink density).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé qui peut avoir une structure de formule (1) ou de formule (2) : [insert figure] R1, R2 étant indépendamment H ou alkyle ou alkylaryle ou X1 ou X2 ; X1, X2 étant indépendamment [insert figure], [insert figure], [insert figure] ou [insert figure] ; et Y1 étant alkyle en C1-C5 ou isoalkyle ; Y3 étant H or alkyle en C1-C3 ; et n étant 1 à 10. Le composé peut être incorporé dans une composition adhésive pour ajuster un profil de propriété souhaité de l'adhésif.
PCT/US2023/065944 2022-04-29 2023-04-19 Nouveau composé d'origine biologique, procédé de formation du composé et compositions adhésives contenant le nouveau composé WO2023212495A1 (fr)

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US63/363,906 2022-04-29

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4299970A (en) * 1974-11-29 1981-11-10 Beecham Group Limited Oxy-alkylamino carboxylic esters

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4299970A (en) * 1974-11-29 1981-11-10 Beecham Group Limited Oxy-alkylamino carboxylic esters

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ARTHUR H. G. DAVID; PABLO GARCÍA‐CEREZO; ARACELI G. CAMPAÑA; FRANCISCO SANTOYO‐GONZÁLEZ; VICTOR BLANCO: "[2]Rotaxane End‐Capping Synthesis by Click Michael‐Type Addition to the Vinyl Sulfonyl Group", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 25, no. 24, 1 April 2019 (2019-04-01), DE, pages 6170 - 6179, XP071848664, ISSN: 0947-6539, DOI: 10.1002/chem.201900156 *
FALORNI, M. ET AL.: "A new diketopiperazine tetra-carboxylic acid as template for the homogeneous phase synthesis of chemical libraries", TETRAHEDRON LETTERS, vol. 38, no. 26, 1997, pages 4663 - 4666, XP004074862, DOI: 10.1016/S0040-4039(97)00961-1 *
KILGORE HENRY R., OLSSON CHASE R., D’ANGELO KYAN A., MOVASSAGHI MOHAMMAD, RAINES RONALD T.: "n →π* Interactions Modulate the Disulfide Reduction Potential of Epidithiodiketopiperazines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 142, no. 35, 2 September 2020 (2020-09-02), pages 15107 - 15115, XP093104615, ISSN: 0002-7863, DOI: 10.1021/jacs.0c06477 *
TAKAHASHI SHU, KIMISHIMA AOI, HIROSE TOMOYASU, YAMADA TAKESHI, SUGAWARA AKIHIRO, SHIRAHATA TATSUYA, NOGUCHI YOSHIHIKO, IWATSUKI MA: "Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 67, 1 March 2021 (2021-03-01), Amsterdam , NL , pages 152895, XP093104619, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2021.152895 *

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